Phenylboronic Acid → Thieno[3,2-d]pyrimidine-6-carboxylic acid, 2-(methylthio)-7-phenyl-, methyl ester

HRID 518783Notes

Reaction equation

HRID 518783 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[S:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[C:9](OS(C(F)(F)F)(=O)=O)[C:7]=2[N:8]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CC(N=P(N1CCCC1)(N1CCCC1)N1CCCC1)(C)C>Cl[Pd]Cl.O1CCOCC1>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[S:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[C:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:7]=2[N:8]=1

Participants

6

Reactant 3

HCID 66827Phenylboronic AcidHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneHCID 86697952HCID 86697952, compound

Product 1

HCID 86697951Thieno[3,2-d]pyrimidine-6-carboxylic acid, 2-(methylthio)-7-phenyl-, methyl esterYield 78.6%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Anhydrous dioxane is added, under argon, to a mixture of 2.5 g of methyl 2-(methylsulfanyl)-7-{[(trifluoromethyl)sulfonyl]oxy}thieno[3,2-d]pyrimidine-6-carboxylate 4 (example 1) and 0.785 g of phenylboronic acid. After the addition of 250 mg of dichloropalladium (dppf) and 4.09 g of BTPP, the mixture is refluxed for 20 h, and then cooled to ambient temperature. The mixture is filtered on silica gel, elution being carried out with ethyl acetate. The solvent is evaporated off under vacuum and the residue is triturated with an ethyl acetate/heptane mixture so as to obtain 1.6 g of methyl 2-(methylsulfanyl)-7-phenylthieno[3,2-d]pyrimidine-6-carboxylate in the form of a whitish precipitate.

Workup

  1. temperaturethe mixture is refluxed for 20 h
  2. filtrationThe mixture is filtered on silica gel, elution
  3. customThe solvent is evaporated off under vacuum
  4. customthe residue is triturated with an ethyl acetate/heptane mixture so as

Sources & evidence

ORD record
ord-1ab7a8cf87c04e34a5341b129eba1404
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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